2-alkyl quaternary ammonium compounds



United States Patent 3,535,380 Z-ALKYL QUATERNARY AMMONIUM COMPOUNDS Zdzislaw W. Dudzinski, Hasbrouck Heights, N.J., and Reginald L. Wakeman, Philadelphia, Pa., assignors to Millmaster Onyx Corporation, New York, N.Y., a corporation of New York No Drawing. Continuation-impart of application Ser. No. 595,349, Nov. 18, 1966. This application Feb. 5, 1968, Ser. No. 703,191

Int. Cl. C07c 87/00 US. Cl. 260567.6 1 Claim ABSTRACT OF THE DISCLOSURE This invention relates to germicidal quaternary ammonium compounds having the formula:

ROHCHa wherein R is a straight-chain alkyl having an even number of carbon atoms between 12 and 14, R and R" are lower alkyls, R is a member of the group consisting of benzyl, alkyl-subsituted benzyl wherein the alkyl contains l to carbon atoms, halo-substituted benzyl, and menaphthyl, and wherein X is a halide.

This invention relates to quaternary amonium compounds, and it particularly relates to such compounds wherein the nitrogen is directly linked to the penultimate carbon atom of the starting hydrocarbon.

This is a continuation-in-part of co-pending application Ser. No. 595,349, filed Nov. 18, 1966 now abandoned.

The quaternary ammonium compounds embodying the present invention have the structure:

wherein R is a straight-chain alkyl having an even number of carbon atoms between 12 and 14, R and R are lower alkyls, preferably either methyl or ethyl, R is a member of the group consisting of benzyl, alkyl-substituted benzyl wherein the alkyl contains 1 to 5 carbon atoms, halo-substituted benzyl, and menaphthyl, and wherein X is a halide.

It has now been discovered that when R contains an even number of carbon atoms, between 12 and 16, these compounds form unexpectedly potent germicidal quaternary compounds.

These quaternary ammonium compounds, which are prepared from 2-alkyl amines, are unexpectedly far superior to those prepared from l-alkyl amines insofar as concerns their microbiocidal properties. Furthermore, the C and C 2-a1kyl quaternaries are more biocidally active than other adjacent homologs.

The following examples are illustrative of the present invention but are not intended to limit the invention except as claimed:

EXAMPLE 1 1 gram equivalent Weight of dimethyl-2 amino hexadecane was reacted with 0.98 gram equivalent weight of benzyl chloride, in an equal weight of 20% isopropanol in distilled water by agitating and heating to 80 C., under ice reflux in a round-bottom flask for about 1 hour, or until no further reaction occurred, as measured by argentometric titration of the ionic chlorine. Reaction was about complete as dimethyl benzyl Z-hexadecyl ammonium chloride, and also present was about 3% of dimethyl 2-hexadecyl amine hydrochloride. Suflicient sodium hydroxide was added to liberate the amine, and an amount of benzyl chloride sufficient to quaternize the latter was added. The reaction was then continued for about one-half hour at the end of which time the quaternization was essentially completed.

EXAMPLE 2 Using the same procedures as in Example 1, but substituting equivalent amounts of the dodecyl, tetradecyl and octadecyl amine homologs, the corresponding dimethyl benzyl 2-alkyl ammonium chlorides were prepared.

The Z-alkyl quaternary ammonium chlorides of Examples 1 and 2 were tested for microbiocidal activity in comparison with the corresponding l-alkyl quaternary ammonium chlorides, using the standard Phenol Coefiicient Method as described in the Oflicial Methods of Analysis of the Association of Oflicial Agricultural Chemists, 9th Edition, pages 63-65, against Staphylococcus aureus and Salmonella typhosa.

Using, as examples of the respective Z-alkyl and l-alkyl compounds, the Z-hexadecyl quaternary, as prepared above, and the corresponding l-hexadecyl quaternary, the microbiocidal results, expressed as phenol coefficients, were as follows:

Dimethyl benzyl Dimethyl benzyl l-amino Z-amino hexadecyl hexadecyl ammoammonium chloride: nium chloride S. aureus 1330 580 S. typhosa 777 640 The same procedure was used to compare the corresponding 2-dodecyl, 2-tetradecyl, Z-hexadecyl, and 2 From the above, it can be seen that there is a spectacular and most unexpected jump in biocidal activity between the dodecyl and the tetradecyl compounds. The hexadecyl compounds are even more germicidally active than the tetradecyl.

The above results make it clear that quaternaries prepared from the 2-alkyl amines are unexpectedly far superior to those prepared from the l-alkyl amines. Furthermore, the C and C 2-alkyl quaternaries are so much more biocidally active than the C homolog that it amounts to a dilference of kind, especially in view of the rapid decline between the C and C homologs.

In addition to using benzyl chloride to form the quaternaries, it is also within the scope of the present invention to use substituted benzyl chlorides wherein the benzyl ring may be substituted in any one or all positions by an alkyl group having from 1 to 5 carbon atoms, or by a halogen such, as chlorine or bromine; or a menaphthyl compound such as a halomethyl naphthylene, exemplified by alphachloromethyl naphthylene, may advantageously be used.

Obviously, many modifications of the present invention are possible in the light of the above teachings. It is,

therefore, to be understood that within the scope of the References Cited appended claim, the invention may be practiced otherwise UNITED STATES PATENTS than as specifically described.

The invention claimed 3,287,410 11/1966 DlldZlIlSkl et al. 260583 A compound having the f l 5 2,692,286 10/ 1954 Stayner 260567.6

Q BERNARD HELFIN, Primary Examiner F M. W. GLYNN, Assistant Examiner R-CH-CHa wherein R is dOdecyl or tetradecyl, R and R are methyl, 10 CL R is benzyl, and X is chloride. 424-329 

